US2196188A - Process of producing formaldehyde - Google Patents
Process of producing formaldehyde Download PDFInfo
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- US2196188A US2196188A US117416A US11741636A US2196188A US 2196188 A US2196188 A US 2196188A US 117416 A US117416 A US 117416A US 11741636 A US11741636 A US 11741636A US 2196188 A US2196188 A US 2196188A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
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- vA still further object is to provide a novel method for effecting the partial oxidation of gaseous hydrocarbons to produce g aldehydes and alcohols and especially for the oxidation of methane to produce formaldehyde or methanol.
- Figure 1 is a longitudinal cross-section view of one embodiment of our invention and Figure 2 is a longitudinal cross-section view of another embodiment thereof.
- the types of apparatus illustrated by Figures 1 and 2 may be advantageously employed in practicing our improved method for carrying out gaseous reactions.
- the surface/volume ratio and the thickness .of the 43 partition may be chosen so that the gases have. reacted to the desired extent by the time they reach the low pressure side of the partition when'ce they are rapidly removed and cooled or otherwisetreated to isolate the reaction prodw ucts.
- the porous partition is maintained at a suitable temperature favorable to the'reaction in question, for example, by radiation from the walls of a surrounding 'chamber or by means of electrical resistances embedded in the -partition.
- the partition may take the form of a screen occupying part or the whole of the cross-section of the gas conduit, but preferably we use a porous tubular vessel ,closed at one end and mounted near the other end in the wall of a containing vessel, the arrangement being such that thereaction gas is compelled to traverse the wall of the tube and is then rapidly withdrawn.
- the initial gas mixture may be admitted to the containing vessel an'd a gas discharge pipe pro- 10 vided communicating with the interior of the porous tube together with a throttle valve for v adjusting the pressure within the tube and con'- sequently the rate of flow of the gases'through the walls of the tube. It is also possible to admit the gas to the porous tube and to withdraw it from the containing vessel.
- Figure I shows a longitudinal cross-section view of an apparatus consisting of a porous tul bular vessel I which is closed at one end and is 25. mounted near the other or open end in the wall of a containing vessel 2.
- The-open end of vessel I communicates by means of conduit 3 through the throttle valve 4 to a scrubbing or other system not shown for recovering or otherwise treating the reaction products.
- the containing vessel 2 is provided with an inlet conduit 5 for supplying the reacting gases. Heat may be supplied to the system by any convenient means not shown, for example, by Iexternally heating the walls of vessel 2 or, ii' desired.
- the walls of the porous vessel I may be provided with electrical resistance wires embedded in the porce lain, or other porous material, for heating the walls "to the desired temperature.
- end of vessel I may be supported, if desired, as indicated in the drawing, within containing vessel 2.
- the arrows in the figure indicate the path taken by the gaseous materials as they pass through the apparatus. If desired, the direction of
- Figure II shows a longitudinal cross-section view of an-apparatushaving a porous partition y6 positioned within a tubular vessel 1 at right angles to the axls'of the tubular vessel.
- Vessel l 50 is provided on one sideof the partition with an inlet conduit 8 for delivery of reactant gases and on the other side with an exit conduit 9 for conducting the reaction by-products to any suitable scrubbingor recovery system not shown.
- the closed '40 throttle valve I is inserted in conduit 9 for adjusting the pressure on the discharge side of the partition 5. Heat may be applied to the system by externally heating vessel 1 or by embedding electrical resistances within the partition 6.
- the porous partition may be made of metal gauze or of sintered metal, glaze or silica. It may also be made of a material which is a catalyst for the reaction in question, or such material may be deposited or incorporated in the material of the partition. In some cases it may be desirable to arrange to cool the low pressure side of the partition, for example, by cooling coils or by admitting cold gases.
- Any suitable pressure may be used in carrying out gas reactions with the aid of porous partitions of the kind described, as the latter are only required to withstand the difference in pressure required to give rise to the desired rate of flow of the gases through the partition.
- rate or flow is conveniently regulated by regulating the pressure on the discharge side of the partition by means of a throttle valve as illustrated in the accompanying drawing.
- a porous tube was constructed of a copper gauze support on which was built a layer inch thick of a catalyst consisting of basic zinc chromate prepared according to the method described in the Proceedings of the Royal S0- ciety A vol. 123 (1929), p. 242.
- the tube was inserted in a steel reaction vessel which was electrically heated to 320 C. and water gas at 100 atmospheres pressure was passed into the reaction vessel.
- the uncombined gases and products were withdrawn at such a rate that the time of contact with the catalyst was about 20 seconds. of the maximum based upon equilibrium measurements. With a similar weight of catalyst distributed about the reaction vessel it required a time of approximately ten minutes to obtain the same yield.
- methane Y can be partially oxidized to formaldehyde by means of gaseous' oxygen, either as such or in the form of air, at temperatures of 400'to 600 C., preferably 450 to 550 C., and at a pressure ranging from atmospheric pressure up to, but not exceeding, 20 atmospheres. At higher pressures and lower temperatures the formation of methyl alcohol is favored.
- gaseous' oxygen either as such or in the form of air
- the partial oxidation of methane in our process occurs freely, after the usual short inhibition period, without the aid of catalysts, although if desired, oxidation catalysts may be employed.
- a high ratio of surface to volume in the reaction space is desirable for bringing about a rapid reaction and this may be achieved by passing the reaction mixture through a vessel containing a porous partition as described above and as illustrated by the accompanying drawing.
- a high The yield of methyl alcohol was space velocity should also be used to ensure that the resultants are quickly removed from the re' action zone, i. e., the solid surfaces and their immediate neighborhood, as quickly as possible.
- the residual gas consists mainly of unused hydrocarbon together with any inert gases. such as nitrogen, that were originally present, and some oxides of carbon formadas ,by-products. If the proportion oi.' unused hydrocarbon is sufficiently high, the residual gas, or a portion thereof, may be returned to the process together with suitable amounts of make-up hydrocarbon and oxygen or oxygen-containing gases.
- Example 2 A mixture of 16% methane and 84% of air was passed under a pressure of 5 atmospheres into a reaction chamber heated to 535 C.
- 'Ihe apparatus employed was essentially the same as that illustrated by Figure I, the porous tube being constructed of-unglazed porcelain.
- 'I'he reactant gases were compelled to pass through the walls of the porcelain tube by maintaining a low pressure on the inside of the tube by means of a throttle valve on the gas discharge pipe.
- the gases emerging from the unglazed porcelain tube were scrubbed vwith water to absorb formaldehyde.
- the yield of formaldehyde obtained was 25% of the methane oxidized. Good yields of formaldehyde were also obtained when working at pressures of 10 atmospheres.
- Example 3 A mixture of of methane and 10% air was passed under a pressure of atmospheres through a reaction chamber of the kind used in Example 2, the temperature being maintained at 300 to 400 C. 'I'he reaction gases ⁇ were cooled- 'I'he process which comprises compelling a' gaseous mixture containing approximately equimolecular quantities of methane and oxygen to pass through a porous partition o f unglazed porcelain at a pressure of 1 to 20 atmospheres and at a temperature of 400-600 C., rapidly withdrawing reaction, products as they emerge f'from said porous partition and separating form- 'aldehyde therefrom,
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Description
Patented Apr. 9, 1940 UNITED STATES PROCESS F PRODUCING FORMALDEHYDE William Arthur Bone and Dudley Maurice Newitt, South Kensington, London, England, assgnors to Imperial Chemical Industries Limited, a corporation of Great Britain 'Application December 23, 1936, Serial No. 117,416 In Great Britain December 24, 1935 1 Claim. (Cl. 26o-604) This' invention relates to a method for effect- It is an object of the present invention to prof f vide a method for carrying out gaseous chemical reactions,'in particular, gaseous reactions-which are dependent upon the presence of solid cata- I .o ly'sts or extended solid surfaces, whereby the reaction products are rapidly removed from the zone of reaction. vA still further object is to provide a novel method for effecting the partial oxidation of gaseous hydrocarbons to produce g aldehydes and alcohols and especially for the oxidation of methane to produce formaldehyde or methanol. These and other objects will be apparent from the ensuing description ofthe invention. v
n Figure 1 is a longitudinal cross-section view of one embodiment of our invention and Figure 2 is a longitudinal cross-section view of another embodiment thereof. The types of apparatus illustrated by Figures 1 and 2 may be advantageously employed in practicing our improved method for carrying out gaseous reactions.
The above objects may be accomplished in accordance with the present invention by causing the reaction gases to flow through a porous partition made of unglazed porcelain, earthenware or other porous material offering an appreciable resistance to the passage of the gases.
The' degree .of porosity of the partition. the
surface/volume ratio and the thickness .of the 43 partition, may be chosen so that the gases have. reacted to the desired extent by the time they reach the low pressure side of the partition when'ce they are rapidly removed and cooled or otherwisetreated to isolate the reaction prodw ucts.
' The porous partition is maintained at a suitable temperature favorable to the'reaction in question, for example, by radiation from the walls of a surrounding 'chamber or by means of electrical resistances embedded in the -partition.
'Ihe partition may take the form of a screen occupying part or the whole of the cross-section of the gas conduit, but preferably we use a porous tubular vessel ,closed at one end and mounted near the other end in the wall of a containing vessel, the arrangement being such that thereaction gas is compelled to traverse the wall of the tube and is then rapidly withdrawn. Thus the initial gas mixture may be admitted to the containing vessel an'd a gas discharge pipe pro- 10 vided communicating with the interior of the porous tube together with a throttle valve for v adjusting the pressure within the tube and con'- sequently the rate of flow of the gases'through the walls of the tube. It is also possible to admit the gas to the porous tube and to withdraw it from the containing vessel.
The present invention may be better understood by referenc to the accompanying drawing which illustrates two types of apparatus that may be advantageously employed in practicing the present invention.
Figure I shows a longitudinal cross-section view of an apparatus consisting of a porous tul bular vessel I which is closed at one end and is 25. mounted near the other or open end in the wall of a containing vessel 2. The-open end of vessel I communicates by means of conduit 3 through the throttle valve 4 to a scrubbing or other system not shown for recovering or otherwise treating the reaction products. The containing vessel 2 is provided with an inlet conduit 5 for supplying the reacting gases. Heat may be supplied to the system by any convenient means not shown, for example, by Iexternally heating the walls of vessel 2 or, ii' desired. the walls of the porous vessel I may be provided with electrical resistance wires embedded in the porce lain, or other porous material, for heating the walls "to the desired temperature. end of vessel I may be supported, if desired, as indicated in the drawing, within containing vessel 2. The arrows in the figure indicate the path taken by the gaseous materials as they pass through the apparatus. If desired, the direction of ow may be reversed;f
Figure II shows a longitudinal cross-section view of an-apparatushaving a porous partition y6 positioned within a tubular vessel 1 at right angles to the axls'of the tubular vessel. Vessel l 50 is provided on one sideof the partition with an inlet conduit 8 for delivery of reactant gases and on the other side with an exit conduit 9 for conducting the reaction by-products to any suitable scrubbingor recovery system not shown. A
The closed '40 throttle valve I is inserted in conduit 9 for adjusting the pressure on the discharge side of the partition 5. Heat may be applied to the system by externally heating vessel 1 or by embedding electrical resistances within the partition 6.
Instead of making the porous partition of unglazed porcelain, earthenware or the like, it may be made of metal gauze or of sintered metal, glaze or silica. It may also be made of a material which is a catalyst for the reaction in question, or such material may be deposited or incorporated in the material of the partition. In some cases it may be desirable to arrange to cool the low pressure side of the partition, for example, by cooling coils or by admitting cold gases.
Any suitable pressure may be used in carrying out gas reactions with the aid of porous partitions of the kind described, as the latter are only required to withstand the difference in pressure required to give rise to the desired rate of flow of the gases through the partition. Such rate or flow is conveniently regulated by regulating the pressure on the discharge side of the partition by means of a throttle valve as illustrated in the accompanying drawing.
Our invention may be illustrated by the following example.
Eample 1 A porous tube was constructed of a copper gauze support on which was built a layer inch thick of a catalyst consisting of basic zinc chromate prepared according to the method described in the Proceedings of the Royal S0- ciety A vol. 123 (1929), p. 242. The tube was inserted in a steel reaction vessel which was electrically heated to 320 C. and water gas at 100 atmospheres pressure was passed into the reaction vessel. The uncombined gases and products were withdrawn at such a rate that the time of contact with the catalyst was about 20 seconds. of the maximum based upon equilibrium measurements. With a similar weight of catalyst distributed about the reaction vessel it required a time of approximately ten minutes to obtain the same yield.
We have found that by our method methane Y can be partially oxidized to formaldehyde by means of gaseous' oxygen, either as such or in the form of air, at temperatures of 400'to 600 C., preferably 450 to 550 C., and at a pressure ranging from atmospheric pressure up to, but not exceeding, 20 atmospheres. At higher pressures and lower temperatures the formation of methyl alcohol is favored.
For formaldehyde production, the methane and oxygen in the reaction mixture are adjusted.
in about equimolecular proportions, kwhile for methanol productionthe ratio of methane to oxygen should be increased. Reaction mixtures in both cases contain sufficient methane to render them non-explosive. A
The partial oxidation of methane in our process occurs freely, after the usual short inhibition period, without the aid of catalysts, although if desired, oxidation catalysts may be employed. A high ratio of surface to volume in the reaction space is desirable for bringing about a rapid reaction and this may be achieved by passing the reaction mixture through a vessel containing a porous partition as described above and as illustrated by the accompanying drawing. A high The yield of methyl alcohol was space velocity should also be used to ensure that the resultants are quickly removed from the re' action zone, i. e., the solid surfaces and their immediate neighborhood, as quickly as possible.
By using gas mixtures containing a limited amount of oiwgen, it is possible to arrange that practically all the oxygen is used up in the short time available for the reaction, and consequently after .the condensible reaction products have been removed from the gases, for example, by cooling, the residual gas consists mainly of unused hydrocarbon together with any inert gases. such as nitrogen, that were originally present, and some oxides of carbon formadas ,by-products. If the proportion oi.' unused hydrocarbon is sufficiently high, the residual gas, or a portion thereof, may be returned to the process together with suitable amounts of make-up hydrocarbon and oxygen or oxygen-containing gases.
Ethane and ethylene behave in a similar manner to methane when submitted to partial oxidation under the conditions described above, although the reaction products are more varied.
The preparation of partial oxidation products of hydrocarbons is illustrated bythe following examples.
Example 2 A mixture of 16% methane and 84% of air was passed under a pressure of 5 atmospheres into a reaction chamber heated to 535 C. 'Ihe apparatus employed was essentially the same as that illustrated by Figure I, the porous tube being constructed of-unglazed porcelain. 'I'he reactant gases were compelled to pass through the walls of the porcelain tube by maintaining a low pressure on the inside of the tube by means of a throttle valve on the gas discharge pipe. The gases emerging from the unglazed porcelain tube were scrubbed vwith water to absorb formaldehyde. The yield of formaldehyde obtained was 25% of the methane oxidized. Good yields of formaldehyde were also obtained when working at pressures of 10 atmospheres.
Example 3 A mixture of of methane and 10% air was passed under a pressure of atmospheres through a reaction chamber of the kind used in Example 2, the temperature being maintained at 300 to 400 C. 'I'he reaction gases` were cooled- 'I'he process which comprises compelling a' gaseous mixture containing approximately equimolecular quantities of methane and oxygen to pass through a porous partition o f unglazed porcelain at a pressure of 1 to 20 atmospheres and at a temperature of 400-600 C., rapidly withdrawing reaction, products as they emerge f'from said porous partition and separating form- 'aldehyde therefrom,
WILLIAM ARTHUR norm. DUDLEY MAURICE NEwrII.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2196188X | 1935-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2196188A true US2196188A (en) | 1940-04-09 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US117416A Expired - Lifetime US2196188A (en) | 1935-12-24 | 1936-12-23 | Process of producing formaldehyde |
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| US (1) | US2196188A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2521538A (en) * | 1945-06-20 | 1950-09-05 | Texaco Development Corp | Process for synthesis of hydrocarbons and the like |
| US2667513A (en) * | 1950-04-03 | 1954-01-26 | Union Oil Co | Manufacture of formaldehyde |
| US20060035986A1 (en) * | 2004-07-29 | 2006-02-16 | Bichkov Oleg V | Method of and apparatus for producing methanol |
| US20060122283A1 (en) * | 2004-07-29 | 2006-06-08 | Pawlak Nathan A | Method of and apparatus for producing methanol |
| US20060154995A1 (en) * | 2004-07-29 | 2006-07-13 | Pawlak Nathan A | Method and apparatus for producing methanol with hydrocarbon recycling |
| US20060204413A1 (en) * | 2004-07-29 | 2006-09-14 | Gas Technologies Llc | Method and apparatus for producing methanol |
| US20060223892A1 (en) * | 2004-07-29 | 2006-10-05 | Gas Technologies Llc | Scrubber for methanol production system |
| US20070166212A1 (en) * | 2005-12-27 | 2007-07-19 | Gas Technologies Llc | Tandem Reactor System Having an Injectively-Mixed Backmixing Reaction Chamber, Tubular-Reactor, and Axially Movable Interface |
| US20070196252A1 (en) * | 2004-07-29 | 2007-08-23 | Gas Technologies Llc | System For Direct-Oxygenation of Alkane Gases |
| WO2007133309A2 (en) * | 2006-05-11 | 2007-11-22 | Gas Technologies Llc | Tandem reactor system having an injectively-mixed backmixing reaction chamber, tubular-reactor, and axially movable interface |
| US7456327B2 (en) | 2004-07-29 | 2008-11-25 | Gas Technologies, Llc | Method for direct-oxygenation of alkane gases |
| US20090118553A1 (en) * | 2005-12-27 | 2009-05-07 | Pawlak Nathan A | Method for direct-oxygenation of alkane gases |
| US7910787B2 (en) | 2004-07-29 | 2011-03-22 | Gas Technologies Llc | Method and system for methanol production |
-
1936
- 1936-12-23 US US117416A patent/US2196188A/en not_active Expired - Lifetime
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2521538A (en) * | 1945-06-20 | 1950-09-05 | Texaco Development Corp | Process for synthesis of hydrocarbons and the like |
| US2667513A (en) * | 1950-04-03 | 1954-01-26 | Union Oil Co | Manufacture of formaldehyde |
| US7910787B2 (en) | 2004-07-29 | 2011-03-22 | Gas Technologies Llc | Method and system for methanol production |
| US20060223892A1 (en) * | 2004-07-29 | 2006-10-05 | Gas Technologies Llc | Scrubber for methanol production system |
| US7578981B2 (en) | 2004-07-29 | 2009-08-25 | Gas Technologies Llc | System for direct-oxygenation of alkane gases |
| US20060204413A1 (en) * | 2004-07-29 | 2006-09-14 | Gas Technologies Llc | Method and apparatus for producing methanol |
| US7642293B2 (en) | 2004-07-29 | 2010-01-05 | Gas Technologies Llc | Method and apparatus for producing methanol with hydrocarbon recycling |
| US7179843B2 (en) | 2004-07-29 | 2007-02-20 | Gas Technologies Llc | Method of and apparatus for producing methanol |
| US9180426B2 (en) | 2004-07-29 | 2015-11-10 | Gas Technologies, Llc | Scrubber for methanol production system |
| US8293186B2 (en) | 2004-07-29 | 2012-10-23 | Gas Technologies Llc | Method and apparatus for producing methanol |
| US20070196252A1 (en) * | 2004-07-29 | 2007-08-23 | Gas Technologies Llc | System For Direct-Oxygenation of Alkane Gases |
| US8202916B2 (en) | 2004-07-29 | 2012-06-19 | Gas Technologies Llc | Method of and apparatus for producing methanol |
| US20060035986A1 (en) * | 2004-07-29 | 2006-02-16 | Bichkov Oleg V | Method of and apparatus for producing methanol |
| US7456327B2 (en) | 2004-07-29 | 2008-11-25 | Gas Technologies, Llc | Method for direct-oxygenation of alkane gases |
| US20060122283A1 (en) * | 2004-07-29 | 2006-06-08 | Pawlak Nathan A | Method of and apparatus for producing methanol |
| US20060154995A1 (en) * | 2004-07-29 | 2006-07-13 | Pawlak Nathan A | Method and apparatus for producing methanol with hydrocarbon recycling |
| US8524175B2 (en) | 2005-12-27 | 2013-09-03 | Gas Technologies Llc | Tandem reactor system having an injectively-mixed backmixing reaction chamber, tubular-reactor, and axially movable interface |
| US20090118553A1 (en) * | 2005-12-27 | 2009-05-07 | Pawlak Nathan A | Method for direct-oxygenation of alkane gases |
| US7687669B2 (en) | 2005-12-27 | 2010-03-30 | Gas Technologies Llc | Method for direct-oxygenation of alkane gases |
| US20110127037A1 (en) * | 2005-12-27 | 2011-06-02 | Gas Technologies Llc | Method and System for Methanol Production |
| US7879296B2 (en) | 2005-12-27 | 2011-02-01 | Gas Technologies Llc | Tandem reactor system having an injectively-mixed backmixing reaction chamber, tubular-reactor, and axially movable interface |
| JP2009521529A (en) * | 2005-12-27 | 2009-06-04 | ガス テクノロジーズ エルエルシー | Method and apparatus for producing methanol |
| US20110116990A1 (en) * | 2005-12-27 | 2011-05-19 | Gas Technologies Llc | Tandem Reactor System Having an Injectively-Mixed Backmixing Reaction Chamber, Tubular-Reactor, and Axially Movable Interface |
| US20100158760A1 (en) * | 2005-12-27 | 2010-06-24 | Gas Technologies Llc | Method and Apparatus for Producing Methanol with Hydrocarbon Recycling |
| US8193254B2 (en) | 2005-12-27 | 2012-06-05 | Gas Technologies Llc | Method and system for methanol production |
| US10287224B2 (en) | 2005-12-27 | 2019-05-14 | Gas Technologies Llc | Method and apparatus for producing methanol with hydrocarbon recycling |
| US20070166212A1 (en) * | 2005-12-27 | 2007-07-19 | Gas Technologies Llc | Tandem Reactor System Having an Injectively-Mixed Backmixing Reaction Chamber, Tubular-Reactor, and Axially Movable Interface |
| WO2007075178A1 (en) * | 2005-12-27 | 2007-07-05 | Gas Technologies Llc | Method and apparatus for producing methanol with hydrocarbon recycling |
| WO2007133309A3 (en) * | 2006-05-11 | 2008-06-05 | Gas Tech Llc | Tandem reactor system having an injectively-mixed backmixing reaction chamber, tubular-reactor, and axially movable interface |
| CN101443113B (en) * | 2006-05-11 | 2012-12-12 | 气体技术有限公司 | Tandem reactor system having an injectively-mixed backmixing reaction chamber, tubular-reactor, and axially movable interface |
| WO2007133309A2 (en) * | 2006-05-11 | 2007-11-22 | Gas Technologies Llc | Tandem reactor system having an injectively-mixed backmixing reaction chamber, tubular-reactor, and axially movable interface |
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